Molecules 2012, 17(10), 12102-12120; doi:10.3390/molecules171012102
Article

Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution

Department of Chemistry, University of Turku, FIN-20014 Turku, Finland
* Author to whom correspondence should be addressed.
Received: 12 September 2012; in revised form: 12 October 2012 / Accepted: 12 October 2012 / Published: 16 October 2012
(This article belongs to the Special Issue Nucleic Acid Analogs)
PDF Full-text Download PDF Full-Text [479 KB, uploaded 16 October 2012 11:28 CEST]
Abstract: Novel soluble supports for oligonucleotide synthesis 11ac have been prepared by immobilizing a 5′-O-protected 3′-O-(hex-5-ynoyl)thymidine (6 or 7) to peracetylated or permethylated 6-deoxy-6-azido-β-cyclodextrins 10a or 10b by Cu(I)-promoted 1,3-dipolar cycloaddition. The applicability of the supports to oligonucleotide synthesis by the phosphoramidite strategy has been demonstrated by assembling a 3′-TTT-5′ trimer from commercially available 5′-O-(4,4′-dimethoxytrityl)thymidine 3′-phosphoramidite. To simplify the coupling cycle, the 5′-O-(4,4′-dimethoxytrityl) protecting group has been replaced with an acetal that upon acidolytic removal yields volatile products. For this purpose, 5′-O-(1-methoxy-1-methylethyl)-protected 3′-(2-cyanoethyl-N,N-diisopropyl-phosphoramidite)s of thymidine (5a), N4-benzoyl-2′-deoxycytidine (5b) and N6-benzoyl-2′-deoxyadenosine (5c) have been synthesized and utilized in synthesis of a pentameric oligonucleotide 3′-TTCAT-5′ on the permethylated cyclodextrin support 11c.
Keywords: cyclodextrin; oligonucleotides; phosphoramidites; soluble support; synthesis

Article Statistics

Load and display the download statistics.

Citations to this Article

Cite This Article

MDPI and ACS Style

Molina, A.G.; Kungurtsev, V.; Virta, P.; Lönnberg, H. Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution. Molecules 2012, 17, 12102-12120.

AMA Style

Molina AG, Kungurtsev V, Virta P, Lönnberg H. Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution. Molecules. 2012; 17(10):12102-12120.

Chicago/Turabian Style

Molina, Alejandro G.; Kungurtsev, Vyacheslav; Virta, Pasi; Lönnberg, Harri. 2012. "Acetylated and Methylated β-Cyclodextrins as Viable Soluble Supports for the Synthesis of Short 2′-Oligodeoxyribo-nucleotides in Solution." Molecules 17, no. 10: 12102-12120.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert